Instead of Core 2 learning that route it picks up a route pointing back to Core 1 creating a nice routing loop. I was aiming for Core 2 to fire that IP out of its default route (which is 172.16.0.254) where 192.168.100.X resides.

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Core2 has learned that route via Core1 and it doesn't have a more specific route in its own routing table to that subnet, so it will send traffic back to Core1 as that's where it thinks it needs to go to. The problem is that routing updates don't include the actual gateway address - they include the subnet only and the sending router's interface IP is used as the gateway, so you redistributing static routes isn't doing what you think it's doing.

When a route is received it is basically an announcement from the sending router that it can reach the specified destination. The interface IP of the sending router is therefore the gateway address for that route. If a similar route is received from a different router its IP address is also a candidate to route traffic for that subnet and that's how we end up with more than one route sometimes.

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